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US4676604A Expired / Lapsed US ⏱️ 0.0 years remaining

Liquid crystals

Assignee: F Hoffmann La Roche AG
•
Filing: 1984-03-05
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Granted: 1987-06-30
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Expires: 2004-03-05
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Abstract

Abstract Compounds of the formula <IMAGE> I wherein R1 is hydrogen or straight-chain alkyl; R2 is -CN, -R, -COR, -COOR or when R2 is positioned on an aromatic ring R2 also can be -OR, -OOCR or -F; R is alkyl; A is a group with 1 to 4 six-membered rings, these rings being linked directly with one another and with ring B in each case via a single covalent bond or being linked at one or two positions also via -COO-, -OOC- or -CH2CH2-; the six-membered rings in A and ring B each are 1,4-phenylene or trans-1,4-cyclohexylene or one of these rings also is trans-2,5-disubstituted m-dioxane, 2,5-disubstituted pyrimidine or 3,6-disubstituted pyridazine, with the proviso that a maximum of two adjacent trans-1,4-cyclohexylene rings are linked directly via a single covalent bond; and m is the integer 2, or when ring B is trans-1,4-cyclohexylene or trans-2,5-disubstituted m-dioxane, m also can be the integer 0, their manufacture, liquid crystalline mixtures which contain these compounds as well as the use of these compounds for electro-optical purposes are described. Additionally, compounds of the formula <IMAGE> LXXVIII wherein R8 is straight-chain C1-C12 alkyl, their manufacture, liquid crystalline mixtures which contain these compounds and their use for electro-optical purposes are described.

Inventors

  • 👤 Martin Petrzilka

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-29 02:54
CPC Classifications
C; C07; C07D; C07D303/00; C07D303/02; C07D303/12; C07D303/18; C07D303/20; C07D303/22; C07C; C07C13/00; C07C13/28; C07C255/00; C07C403/00; C07C403/02; C07C43/00; C07C43/02; C07C43/03; C07C43/14; C07C43/162; C07C43/20; C07C43/215; C07C45/00; C07C45/004; C07C45/27; C07C45/29; C07C45/292; C07C45/56; C07C45/57; C07C45/59; C07C49/00; C07C49/587; C07C49/687; C07C49/76; C07C49/794; C07C49/798; C07C61/00; C07C61/16; C07C61/35; C07D303/04; C07D303/14; C07D303/16; C07D303/38; C07D303/46; C07D317/00; C07D317/08; C07D317/72; C07D319/00; C07D319/04; C07D319/06; C09; C09K; C09K19/00; C09K19/04; C09K19/06; C09K19/08; C09K19/10; C09K19/14; C09K19/20; C09K19/2007; C09K19/30; C09K19/3001; C09K19/34; C09K19/3402; C09K19/3441; C07C2601/00; C07C2601/12; C07C2601/14; C09K2019/3422

Claims Analysis

Total Claims: 27
Claim 1
Independent Claim 145 words
A compound of the formula: ##STR22## wherein R 1 is hydrogen or straight-chain alkyl; R 2 is --CN, --R, --COR, --COOR or when R 2 is positioned on an aromatic ring R 2 also can be --OR, --OOCR or --F; R is alkyl; A is a group with 1 to 4 six-membered rings, A and B rings being linked directly with one another, and rings A in each case being linked via a single covalent bond or being linked at one or two positions also via --COO--, --OOC-- or --CH 2 CH 2 --; the six-membered rings in A and ring B each are 1,4-phenylene or trans-1,4-cyclohexylene, with the proviso that a maximum of two adjacent trans-1,4-cyclohexylene rings are linked directly via a single covalent bond; and m is the integer 2, or when ring B is trans-1,4-cyclohexylene, m also can be the integer 0.
Claim 2
Dependent Claim 145 words
A compound of the formula: ##STR22## wherein R 1 is hydrogen or straight-chain alkyl; R 2 is --CN, --R, --COR, --COOR or when R 2 is positioned on an aromatic ring R 2 also can be --OR, --OOCR or --F; R is alkyl; A is a group with 1 to 4 six-membered rings, A and B rings being linked directly with one another, and rings A in each case being linked via a single covalent bond or being linked at one or two positions also via --COO--, --OOC-- or --CH 2 CH 2 --; the six-membered rings in A and ring B each are 1,4-phenylene or trans-1,4-cyclohexylene, with the proviso that a maximum of two adjacent trans-1,4-cyclohexylene rings are linked directly via a single covalent bond; and m is the integer 2, or when ring B is trans-1,4-cyclohexylene, m also can be the integer 0.
Claim 3
Dependent Claim 90 words
The compound of the claim 1, wherein the compound has the formula: ##STR23## wherein rings B, C and D each are 1,4-phenylene or trans-1,4-cyclohexylene X 1 is a single covalent bond and X 2 is --COO--, --OOC--, --CH 2 CH 2 --, or when at least one of the rings B, C and D is not trans-1,4-cyclohexylene, X 2 also can be a single covalent bond; n is the integer 0 or 1; and R 1 , R 2 , R and m have the significances given in claim 1.
Claim 4
Dependent Claim 10 words
The compound of claim 1, wherein ring B is trans-1,4-cyclohexylene.
Claim 5
Dependent Claim 92 words
The compound of claim 1, wherein the compound has the formula: ##STR24## wherein each of rings B 1 and B 2 is 1,4-phenylene or trans-1,4-cyclohexylene; X 1 is a single covalent bond and X 2 is --COO--, --OOC--, --CH 2 CH 2 --, or when at least one of the rings B 1 and B 2 is not trans-1,4-cyclohexylene, X 2 also can be a single covalent bond; n is the integer 0 or 1; and R 1 , R 2 , R and m have the significances given in claim 1.
Claim 6
Dependent Claim 31 words
The compound of claim 4, wherein X 1 is a single covalent bond; X 2 is a single covalent bond; and each of rings B 1 and B 2 is 1,4-phenylene.
Claim 7
Dependent Claim 11 words
The compound of claim 2, wherein n is the integer 0.
Claim 8
Dependent Claim 14 words
The compound of claim 1, wherein R is straight-chain C 1 -C 12 -alkyl.
Claim 9
Dependent Claim 27 words
The compound of claim 1, wherein R 2 is cyano, alkyl, or when R 2 is positioned on an aromatic ring R 2 also can be alkoxy.
Claim 10
Dependent Claim 35 words
The compound of claim 8, wherein R 2 is cyano, C 3 -C 7 -alkyl, or when R 2 is positioned on an aromatic ring R 2 also can be C 2 -C 6 -alkoxy.
Claim 11
Dependent Claim 23 words
The compound of claim 1, wherein R 1 is hydrogen or straight-chain C 1 -C 10 -alkyl, and m is the integer 0.
Claim 12
Dependent Claim 22 words
The compound of claim 1, wherein R 1 is hydrogen or straight-chain C 1 -C 8 -alkyl, m is the integer 2.
Claim 13
Dependent Claim 23 words
The compound of claim 10, wherein R 1 is hydrogen or straight-chain C 1 -C 5 -alkyl, and m is the integer 0.
Claim 14
Dependent Claim 23 words
The compound of claim 11, wherein R 1 is hydrogen or straight-chain C 1 -C 3 -alkyl, and m is the integer 2.
Claim 15
Dependent Claim 105 words
The compound of claim 1, wherein the compound has the formula: ##STR25## wherein each of rings B 1 , B 2 , B 3 and B 4 is 1,4-phenylene or trans-1,4-cyclohexylene; n is the integer 0 or 1; X 1 is a single covalent bond and each of X 2 , X 3 and X 4 is a single covalent bond, --COO--, --OOC-- or --CH 2 CH 2 --, with the proviso that a maximum of two adjacent trans-1,4-cyclohexylene rings are linked directly via a single covalent bond; and R 1 , R 2 , R and m have the significances given in claim 1.
Claim 16
Dependent Claim 11 words
The compound of claim 14, wherein m is the integer 0.
Claim 17
Dependent Claim 161 words
A liquid crystalline mixture comprising at least two components, wherein at least one component is a compound of the formula: ##STR26## wherein R 1 is hydrogen or straight-chain alkyl; R 2 is --CN, --R, --COR, --COOR or when R 2 is positioned on an aromatic ring R 2 also can be --OR, --OOCR or --F; R is alkyl; A is a group with 1 to 4 six-membered rings, A and B rings being linked directly with one another, and with rings A in each case being linked via a single covalent bond or being linked at one or two positions also via --COO--, --OOC-- or --CH 2 CH 2 --; the six-membered rings in A and ring B each are 1,4-phenylene or trans-1,4-cyclohexylene, with the proviso that a maximum of two adjacent trans-1,4-cyclohexylene rings are linked directly via a single covalent bond; and m is the integer 2, or when ring B is trans-1,4-cyclohexylene, m also can be the integer 0.
Claim 18
Dependent Claim 161 words
A liquid crystalline mixture comprising at least two components, wherein at least one component is a compound of the formula: ##STR26## wherein R 1 is hydrogen or straight-chain alkyl; R 2 is --CN, --R, --COR, --COOR or when R 2 is positioned on an aromatic ring R 2 also can be --OR, --OOCR or --F; R is alkyl; A is a group with 1 to 4 six-membered rings, A and B rings being linked directly with one another, and with rings A in each case being linked via a single covalent bond or being linked at one or two positions also via --COO--, --OOC-- or --CH 2 CH 2 --; the six-membered rings in A and ring B each are 1,4-phenylene or trans-1,4-cyclohexylene, with the proviso that a maximum of two adjacent trans-1,4-cyclohexylene rings are linked directly via a single covalent bond; and m is the integer 2, or when ring B is trans-1,4-cyclohexylene, m also can be the integer 0.
Claim 19
Dependent Claim 347 words
The liquid crystalline mixture of claim 16, wherein the other component is one or more compounds selected from the group consisting of: ##STR27## wherein ring B 1 is 1,4-phenylene or trans-1,4-cyclohexylene; R 9 is straight-chain C 2 -C 7 -alkyl; R 10 is cyano or straight-chain C 1 -C 6 -alkoxy, R 11 is cyano, straight-chain C 1 -C 7 -alkyl or C 1 -C 7 -alkoxy; each of R 12 and R 13 is straight-chain C 1 -C 7 -alkyl; p is the integer 0 or 1; R 14 is trans-4-alkylcyclohexyl, 4'-alkyl-4-biphenylyl, p-(trans-4-alkylcyclohexyl)phenyl, 2-(trans-4-alkylcyclohexyl)ethyl or p-[2-(trans-4-alkylcyclohexyl)ethyl]phenyl and R 15 is trans-4-alkylcyclohexyl; or R 14 is trans-4-alkylcyclohexyl and R 15 is p-(trans-4-alkylcyclohexyl)phenyl, p-[2-(trans-4-alkylcyclohexyl)ethyl]phenyl or 4'-(trans-4-alkyl-cyclohexyl)-4-biphenylyl; or R 14 is p-alkylphenyl and R 15 is p-[2-(trans-4-alkylcyclohexyl)ethyl]phenyl; each of the alkyl groups in R 14 and R 15 is straight-chain C 1 -C 7 -alkyl; one of Z 1 and Z 2 is --COO-- or --OOC-- and the other as well as each of Z 3 and Z 4 are single covalent bonds or one of Z 1 , Z 2 , Z 3 and Z 4 also can be --CH 2 CH 2 --; each of rings B 1 and B 5 in formula XCI is a group of the formula ##STR28## or trans-1,4-cyclohexylene; each of rings B 2 , B 3 and B 4 is a group of formula XCII, or when rings B 2 , B 3 and B 4 are not linked with at least one of the other two of these rings by a single covalent bond, rings B 2 , B 3 and B 4 also can be trans-1,4-cyclohexylene; Y is hydrogen or when Y is positioned on one of the rings of formula XCII which is not linked with a further ring via a single covalent bond, Y also can be fluorine, chlorine or methyl; each of R 16 and R 17 is straight-chain C 1 -C 7 -alkyl or when positioned on a ring of formula XCII R 16 and R 17 also can be straight-chain C 1 -C 7 -alkoxy.
Claim 20
Dependent Claim 28 words
The liquid crystalline mixture of claim 16, wherein the other component is a compound of the formula: ##STR29## wherein R 8 is straight-chain C 1 -C 12 alkyl.
Claim 21
Dependent Claim 177 words
An electro-optical cell comprising: (a) two plate means; (b) liquid crystal means disposed between the two plate means and including a compound of the formula: ##STR30## wherein R 1 is hydrogen or straight-chain alkyl; R 2 is --CN, --R, --COR, --COOR or when R 2 is positioned on an aromatic ring R 2 also can be --OR, --OOCR or --F; R is alkyl; A is a group with 1 to 4 six-membered rings, A and B rings being linked directly with one another, and rings A in each case being linked via a single covalent bond or being linked at one or two positions also via --COO--, --OOC-- or --CH 2 CH 2 --; the six-membered rings in A and ring B each are 1,4-phenylene or trans-1,4-cyclohexylene, with the proviso that a maximum of two adjacent trans-1,4-cyclohexylene rings are linked directly via a single covalent bond; and m is the integer 2, or when ring B is trans-1,4-cyclohexylene, m also can be the integer 0; and (c) means for applying an electrical potential to said plate means.
Claim 22
Dependent Claim 177 words
An electro-optical cell comprising: (a) two plate means; (b) liquid crystal means disposed between the two plate means and including a compound of the formula: ##STR30## wherein R 1 is hydrogen or straight-chain alkyl; R 2 is --CN, --R, --COR, --COOR or when R 2 is positioned on an aromatic ring R 2 also can be --OR, --OOCR or --F; R is alkyl; A is a group with 1 to 4 six-membered rings, A and B rings being linked directly with one another, and rings A in each case being linked via a single covalent bond or being linked at one or two positions also via --COO--, --OOC-- or --CH 2 CH 2 --; the six-membered rings in A and ring B each are 1,4-phenylene or trans-1,4-cyclohexylene, with the proviso that a maximum of two adjacent trans-1,4-cyclohexylene rings are linked directly via a single covalent bond; and m is the integer 2, or when ring B is trans-1,4-cyclohexylene, m also can be the integer 0; and (c) means for applying an electrical potential to said plate means.
Claim 23
Dependent Claim 6 words
The compound of claim 1, p-[trans-4-(trans-1-propenyl)cyclohexyl]benzonitrile.
Claim 24
Dependent Claim 6 words
The compound of claim 1, p-[trans-4-(trans-1-butenyl)cyclohexyl]benzonitrile.
Claim 25
Dependent Claim 6 words
The compound of claim 1, p-[trans-4-(trans-1-pentenyl)cyclohexyl]benzonitrile.
Claim 26
Dependent Claim 6 words
The compound of claim 1, p-[trans-4-(3-butenyl)cyclohexyl]benzonitrile.
Claim 27
Dependent Claim 6 words
The compound of claim 1, p-[trans-4-(trans-3-pentenyl)cyclohexyl]benzonitrile.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1990-06-29 1990-12-29 1991-06-30 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1994-06-29 1994-12-29 1995-06-30 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1998-06-29 1998-12-29 1999-06-30 $7700.00 Window Closed / Lapsed

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